January

Maryland Polar Bear PlungeJanuary 30, 2016. Sandy Point State Park, 1100 East College Parkway, Annapolis. Participants take a chilly dip in the Chesapeake Bay to raise funds for Special Olympics Maryland. Not ready to bare it all? Then join in the festivities—fully clothed—under a huge heated tent that includes vendor booths, live entertainment, zoo animals, food court, carnival amusements, sandcastle building, a “kids’ zone” and more. See Photos of the Maryland Polar Bear Plunge.

February

Annapolis Restaurant WeekFebruary 22- 28, 2016. Take advantage of the opportunity to try that little-known restaurant you've been meaning to sample or indulge at one of your favorites. Enjoy two-course fixed-price breakfasts for $12.95, two-course luncheons for $15.95, and three-course fixed-price dinners for $32.95.

March

Irish Week in AnnapolisMarch 6-17, 2017. Various locations in downtown Annapolis. Plans are in the works for a ten-day celebration in preparation for St. Patrick’s Day. Tentative events include a parade, reenactments, music and an Irish Coffee competition.

March 18-20, 2016. Multiple sites throughout the Four Rivers Heritage Area. Learn about Maryland’s history with family and friends during a fun-filled festival highlighting the uniqueness of the Four Rivers Heritage Area. Local cultural and heritage sites offer special activities and tours. Stroll through downtown Annapolis or visit Historic London Town and the Annapolis Countryside to enjoy educational tours, costumed re-enactors, art exhibits, kids' activities, and more.

Annapolis Oyster Roast & Sock BurningMarch 19, 2016, Noon – 4 p.m. Annapolis Maritime Museum, 723 Second St. Eastport. Celebrate spring with a family-friendly feast of the Chesapeake’s most cherished bivalve. Festivities begin with the annual sock burning and go on to include live music, shucking and cooking demonstrations, an oyster shucking contest, and exhibits highlighting the area’s unique maritime heritage and the role oysters play in maintaining the health of the Bay. Feast on oysters any way you like them – raw, steamed, fried, and grilled.

Annapolis Film FestivalMarch 31-April 3, 2016. Multiple sites - St. John’s College, Maryland Hall, St. Anne’s Parish Hall, Annapolis. The excitement of Hollywood on the Chesapeake returns with more than 65 narrative and documentary films in all genres; Q&A sessions with filmmakers and visiting industry guests; special panels and showcases.

April

Annapolis Beer WeekApril 1-8, 2016. More than 60 unique brands of beer will be available – including some beers offered exclusively during Beer Week. The weeklong event includes: Beer Run, Beer and Bands, and the Maryland Chicken Wing and Beer Fest.

Annapolis Book FestivalApril 16, 2016. The Key School, 534 Hillsmere Drive, Annapolis. The free festival celebrates the beauty, power, passion, and excitement of the written word. It brings nationally renowned authors to The Key School to discuss their books and the craft of writing. The celebration of the written word also features children's activities, live music, a huge used book sale and a coffee shop.

Annapolis Spring Sailboat ShowApril 22-24, 2016. City Dock, Annapolis. The show kicks off the boating season as experienced and novice sailors shop for the latest in equipment, electronics, clothing and boating accessories at the 100+ on-land nautical exhibits and on-site pro surf shops. The springtime show will feature more than 80 new and previously-owned sailboats of all types and sizes – including catamarans, mono hulls, racing boats, inflatables, and day sailors.

Arts in the Park FestivalApril 23, 2016. Chesapeake Arts Center, 194 Hammonds Lane, Brooklyn Park. The family-friendly festival features art, music, dance, theatre and food. The Chesapeake Arts Center will use the occasion to announce the 2015/2016 season and provide some sneak peeks of the performances to come.

May 6-7, 2016. Anne Arundel County Fairgrounds, 1450 Generals Highway, Crownsville. Enjoy live music, abundant food, and a barbeque competition during the family event to benefit Anne Arundel Medical Center’s Pediatric Unit and the Boys & Girls Clubs. Sponsored by the Parole Rotary Club, the celebration includes live music on two stages, activities for all ages, arts and crafts vendors and cooking demonstrations.

May 20-27, 2016. U.S. Naval Academy, Annapolis. Each year, approximately 1,000 midshipmen graduate and receive their commissions as officers in the U.S. Navy or Marine Corps. On Monday, cheer on members of the class of 2018 as they attempt to climb the Herndon Monument. Traditionally, the Blue Angels’ flight rehearsal is on Tuesday and the Blue Angels’ flight demonstration is on Wednesday. On Thursday, catch the Color Parade at Worden field.

June 12, 2016. Throughout Eastport. Explore the gardens and/or interiors of 8-10 select homes within an easy stroll of one another. Tickets are limited. Advance purchase is recommended. Proceeds benefit Eastport community organizations, programs and causes.

Annapolis Fourth of JulyJuly 4, 2016. 6:30 p.m. Downtown Annapolis. The festivities kick off at 6:30 p.m. with an old-fashioned community parade. This patriotic salute to our nation is always a crowd pleaser with thousands of viewers lining the route. The night wraps up with fireworks over Annapolis Harbor starting around 9:15 p.m. See photos of 4th of July in Annapolis.

Annapolis Irish FestivalJuly 15-16, 2016. Anne Arundel County Fairgrounds, 1450 General’s Highway, Crownsville. Celebrate everything Irish at the only festival of its kind in the region. Enjoy traditional Celtic music and Irish rock bands on three different stages, along with workshops and exhibits. When you get hungry, try some delicious Irish beef stew and other Irish favorites. Little Leprechaun Land provides pony rides, face painting and other free activities for the kids.

August

Rotary Club of Annapolis Crab FeastAugust 5, 2016. Navy-Marine Corps Memorial Stadium, 550 Taylor Avenue, Annapolis. Crustacean lovers feast on the Chesapeake Bay’s bounty at this all-you-can-eat and drink event that is arguably the largest crab feast in the world. More than 3,000 people are expected to finish off 320 bushels of crabs, 3,400 ears of corn, 100 gallons of crab soup, 1,800 hot dogs, 150 pounds of beef barbeque, and hundreds of gallons of beer and soft drinks. Proceeds benefit local community and cultural organizations.

August 20, 2016. Eastport Yacht Club, 317 First Street, Annapolis. The Boatyard Regatta benefits Chesapeake Region Accessible Boating (CRAB), a non-profit organization dedicated to making sailing available for people with disabilities. After a glorious day of sailing on the Bay, contestants and well-wishers enjoy food, libation and rockin’ live music in Annapolis’ historic Eastport.

September

Maryland Seafood FestivalSeptember 10-11, 2016. Sandy Point State Park, 1100 East College Parkway, Annapolis. A highlight of the event is the Crab Soup Cook-off, an Annapolis favorite that brings together the city’s greatest restaurateurs and chefs in a classic Maryland showdown.

October 6-10, 2016. The nation’s oldest and largest in-water sailboat show features exclusively new boats attracts more than 50,000 boating enthusiasts from around the world to America’s Sailing Capital each year. The event is recognized worldwide as the premier sailing showcase for seminars, boating attire and accessories, foul weather gear and boats of all sizes.

U.S. Powerboat ShowOctober 13-16, 2016. City Dock, Annapolis. The show includes family cruisers, center consoles, inflatables and the world's largest power catamaran section. Attendees will also find a wide selection of marine equipment, high-tech electronics, accessories, gear, and related services.

Oyster FestivalOctober 16, 2016. Captain Avery Museum, 1418 East West Shady Side Road, Shady Side. Enjoy food, live music by local artists, unique crafts, face painting, live crab races and demonstrations showing the vital role oysters play in maintaining the health of the Chesapeake Bay. Seafood lovers are invited to feast on raw and fried oysters, oyster stew, fried oyster roll sushi, cream of crab soup, Maryland crab soup, and much more. Hamburgers and hot dogs will also be available.

November - December

Maritime Republic of Eastport’s Tug o’ WarNovember 5, 2016. Eastport & Annapolis City Dock. Drawing on a decades-old rivalry, the annual charitable event features the longest tug-of-war over a body of water in the world, pitting downtown Annapolitans against the rebels of the mock-breakaway Maritime Republic of Eastport. Dubbed the Slaughter across the Water, it features a 1700-foot rope, 450 tuggers and 1000 spectators.

Annapolis by CandlelightNovember 4-5, 2016. Historic Homes in Downtown Annapolis. The once a year event offers a peek inside some of the finest homes in Annapolis’ Historic District. Luminaries lead the way to centuries-old homes and public places during a magical self-guided tour. Different homes and neighborhoods are showcased each year.

Mid-November, 2016 to January 1, 2017. Sandy Point State Park, 1100 East College Parkway, Annapolis. The event features more than 60 animated and stationary displays, including traditional Maryland-themed favorites, holiday and children’s displays. Proceeds benefit Anne Arundel Medical Center. See Photos of Lights on the Bay

Grand Illumination – City Tree LightingNovember 27, 2016. Market House, 25 Market Street, Annapolis. Watch Santa arrive in town. Area children's groups will be singing and dancing. The Jaycees will provide hot chocolate, glow sticks and ornaments for children to decorate the tree. They also will be collecting nonperishable food items and new, unwrapped toys for their annual Angel Tree Project, which supports twenty local families in need. Read more about Christmas in Annapolis.

Eastport Yacht Club Lights ParadeDecember 10, 2016. Annapolis Harbor and Spa Creek. Dozens of boats illuminated with thousands of colored lights and crewed by jolly revelers suddenly appear in the cold wintry night. Families and friends gather at their favorite viewing spots along the waterfront to enjoy the yearly spectacle.

Military BowlDecember 27, 2016. U.S. Navy-Marine Corps Memorial Stadium, 550 Taylor Avenue, Annapolis. The Military Bowl® presented by Northrop Grumman, benefiting the USO, will match a team from the Atlantic Coast Conference (ACC) against an opponent from the American Athletic Conference (AAC).